Craig Shapiro of Collaborative Fund and GOOD Talks BankSimple, Drudge Report, Socially-Conscious Investing, and the Start-Up He’d Most Like to See

Craig Shapiro, former president of GOOD magazine and current CEO of the socially-conscious Collaborative Fund, has a place to leave his shoes in New York now. Collaborative is invested in multiple start-ups in the city, including Kickstarter, BankSimple, and SkillShare, and its New York connection is getting stronger–SkillShare founder Mike Karnjanaprakorn recently announced he’d been brought on as a venture adviser. Collaborative is on the verge of hiring its second New York employee, a junior scout sort of position, which Mr. Shapiro says he’ll announce in about two weeks.

There’s some history there, too–Mr. Shapiro learned much of what he knows about start-up investing from Josh Kushner of Thrive Capital. He also invested in New York-based Give Real (alongside early Facebook investor Eduardo Saverin) which attempted peer-to-peer ecommerce on social platforms; it flopped, much to Mr. Shapiro’s dismay.

“I really loved that idea,” he said wistfully over tea at an open-air cafe on Prince St., where Betabeat met with him yesterday morning, where he riffed, at our request, on design, investing and changing the world.

Collaborative’s investment philosophy is pretty simple, he said. The fund–which launched at the end of 2010 with $6 million, but has raised an undisclosed amount more–focuses on companies that encourage collaborative consumption in a way that aligns social benefit with profitability. So far, that hasn’t been easy.

“I do find it challenging to find start-ups that are working on world-changing ideas,” he said. “And a world-changing idea doesn’t need to be solving global poverty. It can be something very simple. But I do think that first-world problems, like not being able to find a parking space–it actually may be a good business opportunity, but it’s not something that I’m really interested in.”

Which big-name start-ups would you invest in if you could? we asked. Would you invest in Tumblr? (He had mentioned Tumblr as an example of a love-mark sort of brand.)

“I’d invest in Tumblr, because of the ease of use and simplicity of design. Instapaper. I think what Marco has done is so cool and I’ve met him and he seems like just a great entrepreneur. He understands how to build products and I think it’s one of the more usable things that’s been built in the past couple years. Drudge Report! He’s so disruptive to the news space and what he’s been able to pull off, I’m like, holy cow. I would love an opportunity to invest in that.

“I would love an opportunity to invest in DonorsChoose, but it’s a nonprofit so there isn’t a clear path as to how I’d make money on that investment,” he added.

Wait, back up, we said. You’d invest in the Drudge Report? Is it because you want to redesign it?

“The design in some ways is charming to me. It brings me back to like when I first started consuming web content, like animated GIFs and big fonts and a hodgepodge of somebody who had just learned html. I’d be afraid if we redesigned it, that it would lose some of that charm. I don’t know. It’s so functional that it’s hard to argue with.”

Same with Craigslist, he added.

But as far as companies he is invested in, he’s very bullish on Brooklyn-based BankSimple, which is attempting to disrupt consumer banking with a single bank card that works in any ATM and an online-only interface.

“In the four years that I’ve been investing, I’ve never seen a product with more anticipation than BankSimple,” he said. “There’s so much pent-up interest and curiosity, it’s crazy. I field more questions about what they’re up to than virtually any other company that I’ve ever even worked for or invested in…

“I love the idea of using transparency as a weapon to compete with. They’re just like, ‘we’re going to make this dead simple from a user experience perspective, and our fees are going to be totally transparent. We’re not going to nickel and dime, we’re not going to have hidden fees, we’re going to out-compete Citibank and Chase by creating a more consumer friendly experience,'” he said.

But it’s tough, being disruptive. (Maybe this is why people make apps to track open parking spaces and unused frequent flier miles?) BankSimple has had challenges coming to market, he said, which is frustrating. The launch, which was supposed to happen in the spring, is delayed, and the start-up’s lead engineer recently quit.

There’s another start-up that’s struggling to get off the ground; or rather, out of Mr. Shapiro’s head. “It’s a secret,” he said. “But I’ll tell you. It’s on the record but it’s totally secret.”

We had the feeling this was one idea Mr. Shapiro would be happy to have stolen by someone with the time to build it. The idea: A universal reputation score that factors in scores from services like Kiva, Airbnb and eBay–like a Klout score, but for trustworthiness. And in Mr. Shapiro’s imagining, this score would include good deeds as well. Recycling, for example.

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